Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
  • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D207/36—Oxygen or sulfur atoms
  • C07D207/40—2,5-Pyrrolidine-diones
  • C07D207/416—2,5-Pyrrolidine-diones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
  • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
  • C08G65/3324—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof cyclic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
  • C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
  • C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
• • C—CHEMISTRY; METALLURGY
  • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
  • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
  • C10L1/00—Liquid carbonaceous fuels
  • C10L1/10—Liquid carbonaceous fuels containing additives
  • C10L1/14—Organic compounds
  • C10L1/22—Organic compounds containing nitrogen
  • C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
  • C10L1/224—Amides; Imides carboxylic acid amides, imides

Definitions

• This invention concerns N-substituted succinimides, their manufacture and use as additives for gasoline and the resultant improved gasoline compositions having good anti-rust and detergent properties in the carburetor or in the intake systems.
• the accumulation of deposits impedes the normal flow of air through the carburetor and consequently results in the formation of rich fuel mixtures.
• the deposits may be formed, for example, by accumulation of impurities or dusts from air or from the recycle gas from the engine housing.
• the modern fuels require further additives for improving the behaviour of the fuel, such as anti-rust additives and additives for reducing the deposits in the admission system.
• anti-rust additives and additives for reducing the deposits in the admission system.
• multifunctional additives are used.
• the products of the invention can be defined as those obtained by reacting maleic anhydride with at least one oxyalkylated or poly-oxyalkylated monoalcohol of the general formula:
• R 1 is a linear or branched saturated or unsaturated aliphatic radical containing from 12 to 25 carbon atoms, preferably from 12 to 22 carbon atoms
• A is a linear or branched alkylene radical containing from 2 to 4 carbon atoms, at least two of which are in a straight chain and n is an integer from 1 to 50.
• R 2 is a linear or branched, saturated or unsaturated aliphatic radical containing from 8 to 25, preferably from 8 to 22 carbon atoms
• Z is a linear or branched alkylene radical containing from 2 to 4 carbon atoms, at least two of which are in a straight chain
• X is either a --NH-- group or an oxygen atom --O--
• m is an integer from 0 to 4.
• the product of the first reaction may be reacted with a bi-primary amine of the general formula:
• Z is defined as above and p is an integer from 2 to 6.
• the product resulting from the reaction of maleic anhydride with an oxyalkylated or poly-oxyalkylated monoalcohol of formula (I) may be considered as having a formula of the type: ##STR1## wherein R 1 , A and n are defined as above.
• the final product may be considered as having a formula of the type: ##STR3## wherein the letters have the same meaning as above defined and z is an integer equal to p-1.
• the radical R 1 is preferably a linear alkyl radical containing 12 or 13 carbon atoms.
• these products advantageously have their terminal hydroxy group on a secondary or tertiary carbon atom of an alkylene group: the chains of recurrent alkylene units advantageously comprise a terminal propylene oxide group: ##STR4## or an isobutylene oxide group: ##STR5##
• oxyalkylated or poly-oxyalkylated monoalcohols of formula (I) contemplated according to the invention include:
• polyoxypropylated lauric alcohol containing, for example, 21 propylene oxide recurrent units
• the products of the invention can be prepared by condensation of the reactants without solvent, but preferably with a solvent, for example an aromatic hydrocarbon whose boiling point is in the range from 70° C. to 200° C., while removing the water formed during the reaction.
• a solvent for example an aromatic hydrocarbon whose boiling point is in the range from 70° C. to 200° C.
• the reaction temperature is usually from 65° C. to 200° C., preferably from 80° C. to 160° C.
• the reaction lasts from 0.5 to 6 h, preferably from 1 to 3 h.
• the amines of formula (II) are generally used in an amount from 1.02 to 1.2 mole and preferably from 1.05 to 1.1 mole per mole of the anhydride represented by formula (IV).
• the amides of formula (III) are generally used in an amount from 1.02 to 1.2 mole and preferably from 1.05 to 1.1 mole per 2 moles of the anhydride represented by formula (IV).
• the products of the invention may also be obtained by a single step of condensing maleic anhydride the oxyalkylated or polyoxyalkylated monoalcohol of formula (I) and the amine of formula (II) or the amine of formula (III).
• the "ether-N-substituted succinimide" structure of the products according to the invention is ascertained by infra-red spectrometry: the infra-red spectra in fact contain succinimide absorption bands at 1700 cm -1 and ether absorption bands at 1110 cm -1 .
• These products are used as fuel additives. They offer the advantage of multifunctional properties; they have a surface-active action and exhibit good film-forming properties and improve the corrosion resistance of metal parts; in addition, their heat stability is such that they do not contribute by themselves to the formation of deposits and, as a result of their film-forming effect which is maintained at high temperature, they prevent the usual formation of deposits from lubricating oil particles or aromatic or olefinic products decomposed by heat to some extent.
• the products according to the invention may be used in motor fuels at concentrations of, for example, 10 to 500 and preferably 20 to 200 parts per million (ppm) by weight, without occurrence of any trouble, even at low temperature, and they may be associated without disadvantage to other usual additives.
• polypropylene glycol monolauryl-ether i.e. polyoxypropylated lauric alcohol containing about 21 propylene oxide recurrent units per molecule
• polypropylene glycol monolauryl-ether i.e. polyoxypropylated lauric alcohol containing about 21 propylene oxide recurrent units per molecule
• the mixture is again heated for 3 h at reflux at 145° C., with azeotropic distillation of the formed water.
• Example I is repeated, except that a solution of 9.90 g (0.06 mole) of tetraethylenepentamine in 250 ml of xylene is added to the 153.8 g of the oil formed in the first step which constitutes the polypropoxylated succinic anhydride.
• the mixture is heated to reflux for 3 h 30 at 144° C., with azeotropic distillation of the water formed during the reaction.
• the desired product obtained as a 50% solution in xylene, is a triamino-bis(polypropoxylated succinimide) as ascertained by I.R. spectrometry.
• the ISD (Induction System Deposit) process is conducted according to the experimental method developed by the Southwest Research Institute (San Antonio--Texas) by A. A. JOHNSTON and E. DIMITROFF, SAE Transactions, Vol. 75, p. 885-891, Article 660 783 (1969).
• This process provides for the estimation of the heat stability of an additive in solution in a premium gasoline by simulation of its passage on hot surfaces of a running engine and particularly on the intake valve.
• the corrosion test consits of determining the extent of the corrosion produced by synthetic sea water on cylindrical samples of ordinary polished steel, according to modified standard ASTM D 665 (temperature 32.2° C.; duration 20 h.).
• the interfacial tension was measured according to standard ASTM D 971. The results are reported in Table II, which further indicates, by way of comparison, the results obtained with a premium gasoline without additive and those obtained with the premium gasoline containing a conventional additive at a concentration of 0.01% by weight.
• the bench test of carburetor fouling is conducted according to the method BNPe R5 GTL developed by ELF/IFP.
• This method consists of estimating on a combustion engine at bench the capacity of a motor fuel to maintain a carburetor clean.
• the test is performed in 12 hours and comprises 2 periods of 6 hours separated by a stopping period of 18 hours.
• the fouling of the carburetor is enhanced by the recycling to intake of a portion of the exhaust gases.
• a visual appraisal of the state of the carburetor body is expressed by marks from 0 to 10.
• 0 is the mark for a foul carburetor.
• the mark takes into account the presence of deposits, their colour and their position in the carburetor and on the intake butterfly valve.
• the intake valve fouling test at bench is performed according to the method developed by the Research and Development Department of Irish BP Aktiengesellschaft in Hamburg.
• Its object is to determine at the test bench the capacity of the additive-containing fuels to keep the intake valves clean.
• the test consists of equipping a 1.25 Opel Kadett motor with a double carburetor. In this way it is possible to simultaneously test either an additive at two different concentrations, or two different additives or an additive-containing premium gasoline comparatively with the same premium gasoline without additive.
• the test simulates a sequence of driving at normal running speed and at idling conditions at 35, 50 and 80 Km per hour.
• the operation program at the test bench is as follows:

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Polymers & Plastics (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Liquid Carbonaceous Fuels (AREA)
• Pyrrole Compounds (AREA)
• Lubricants (AREA)
• Polyethers (AREA)
• Luminescent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Polyesters Or Polycarbonates (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
• Solid Fuels And Fuel-Associated Substances (AREA)

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Family Applications (1)

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Cited By (11)

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Citations (7)

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• 1980
  • 1980-02-15 FR FR808003459A patent/FR2476119B1/fr not_active Expired
• 1981
  • 1981-02-11 AT AT81400215T patent/ATE6267T1/de not_active IP Right Cessation
  • 1981-02-11 DE DE8181400215T patent/DE3162191D1/de not_active Expired
  • 1981-02-11 EP EP81400215A patent/EP0034968B1/fr not_active Expired
  • 1981-02-13 US US06/234,134 patent/US4422856A/en not_active Expired - Lifetime
  • 1981-02-13 NO NO810497A patent/NO155882C/no unknown
  • 1981-02-13 CA CA000370870A patent/CA1173045A/fr not_active Expired
  • 1981-02-16 JP JP2214281A patent/JPS56150061A/ja active Granted

Patent Citations (7)

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